Guest Stars Maggie Lawson as Natalie Flynn Thomas Lennon as Leo Getz Jonathan Sadowski as Andrew Simon Nishi Munshi as Erica Malick Jessica Tuck as Anna Strong Haley Strode as Julie Don Harvey as Tom Kessler Co Starring Darin Heames as Raymond Katrina Nelson as Saleswoman Elia Cantu as Delilah June Carryl as Judge Patrick Burch as Preston Dieterich Gray as Shep Robert Morgan as Starks Mikayla B. Head as Harper